Design, synthesis and 2D QSAR study of novel pyridine and quinolone hydrazone derivatives as potential antimicrobial and antitubercular agents

Abdelrahman, Mohamed A.; Salama, Ismail; Gomaa, Mohamed S.; Elaasser, Mahmoud M.; Abdel‐Aziz, Marwa M.; Soliman, Dalia H.

doi:10.1016/j.ejmech.2017.07.004

Cited by 83 publications

(38 citation statements)

References 61 publications

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“…In the case of L 3 and L 4 , CÀ H···O and CÀ H···N type H-bonding interactions are present. In L 3 , intermolecular CÀ H···O, H-bonding interaction involves hydrogen atom of pyridine ring (H26) of one molecule and donor oxygen atom of aroyl group of adjacent molecule (O1), with the bond length of C(26) À H(26)···O(1), 2.502(7) Å, whereas CÀ H···N interactions involve hydrogen atom of pyridine ring (H029) of one unit and N atom of an adjacent pyridine ring N(7) of another unit, C(29) À H (029)···N (7), distance = 2.717(1) Å, leading to the formation of a 1-D polymeric chain ( Figure 6). In the case of L 4 , only CÀ H···O type intermolecular hydrogen bonding interactions involve the donor O atom of aroyl group of one molecule and H atom of the benzene ring of an adjacent molecule, C(20)À H(20)···O (1), distance = 2.446(21) Å constructing a 1-D (Figure S19) polymeric chain and these 1-D polymeric chains are coordinated to each other via CÀ H···O type intermolecular hydrogen bonding interactions, involving the donor O atom of aroyl groups of one layer and H atom of benzene rings of the adjacent layer, C(10)À H(10)···O(2), 2.439 (20) Å, leading to the formation of a 2-D network (Figure 7).…”

Section: Molecular Structures Of L 1 -Lmentioning

confidence: 99%

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Design and Construction of Aroyl‐Hydrazone Derivatives: Synthesis, Crystal Structure, Molecular Docking and Their Biological Activities

Kumari

Ansari

Kumar

et al. 2019

Chemistry & Biodiversity

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Here, we report the synthesis and characterization of four new aroyl‐hydrazone derivatives L1–L4, and their structural as well as biological activities have been explored. In addition to docking with bovine serum albumin (BSA) and duplex DNA, the experimental results demonstrate the effective binding of L1–L4 with BSA protein and calf thymus DNA (ct‐DNA) which is in agreement with the docking results. Further biological activities of L1–L4 have been examined through molecular docking with different proteins which are involved in the propagation of viral or cancer diseases. L1 shows best binding affinity with influenza A virus polymerase PB2 subunit (2VY7) with binding energy −11.42 kcal/mol and inhibition constant 4.23 nm, whereas L2 strongly bind with the hepatitis C virus NS5B polymerase (2WCX) with binding energy −10.47 kcal/mol and inhibition constant 21.06 nm. Ligand L3 binds strongly with TGF‐beta receptor 1 (3FAA) and L4 with cancer‐related EphA2 protein kinases (1MQB) with binding energy −10.61 kcal/mol, −10.02 kcal/mol and inhibition constant 16.67 nm and 45.41 nm, respectively. The binding energies of L1–L4 are comparable with binding energies of their proven inhibitors. L1, L3 and L4 can be considered as both 3FAA and 1MQB dual targeting anticancer agents, while L1 and L3 are both 2VY7 and 2WCX dual targeting antiviral agents. On the other side, L2 and L4 target only one virus related target (2WCX). Furthermore, the geometry optimizations of L1–L4 were performed via density functional theory (DFT). Moreover, all four ligands (L1–L4) were characterized by NMR, FT‐IR, ESI‐MS, elemental analysis and their molecular structures were validated by single crystal X‐ray diffraction studies.

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Section: Molecular Structures Of L 1 -Lmentioning

confidence: 99%

“…Aroyl‐hydrazones inhibit metalloproteins, perturbation of intracellular homeostasis by interaction with DNA . Hydrazones based molecules exhibit anti‐inflammatory, antimicrobial, antiplatelet, anticonvulsant, antitubercular, antitumor, antifungal and antiviral activity with a potential to overcome multidrug resistance …”

Section: Introductionmentioning

confidence: 99%

Design and Construction of Aroyl‐Hydrazone Derivatives: Synthesis, Crystal Structure, Molecular Docking and Their Biological Activities

Kumari

Ansari

Kumar

et al. 2019

Chemistry & Biodiversity

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“…Quantitative structure–activity relationship (QSAR) study was carried out to correlate antibacterial activity of a novel series of pyridine and quinolone derivatives …”

Section: Introductionmentioning

confidence: 99%

Quantitative modeling for prediction of thermodynamic properties of some pyridine derivatives using molecular descriptors and genetic algorithm‐multiple linear regressions

Hajibabaei

Shafiei

Abdoli‐Senejani

2019

J Chinese Chemical Soc

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Pyridines are compounds with a wide range of biological activities and they are the basis of several groups of drugs. In this study, the relationship between molecular descriptors and the thermal energy (E th kJ/mol), heat capacity (C v J/molK), entropy (S J/mol K), enthalpy of formation (ΔH f kJ/mol), and Gibbs free energy (ΔG kJ/mol) of pyridine derivatives is studied. These properties were calculated at the Hartree-Fock level of theory and 6-311G* G basis sets by Gaussian 09 software. The chemical structures of 171 pyridine derivatives were drawn by the Gauss View 05 program.The genetic algorithm-multiple linear regression (GA-MLR) and backward methods-were used to select the suitable descriptors and also for predicting the thermodynamic properties of pyridine derivatives. The correlations between the molecular descriptors in the best models were discussed by the Pearson coefficient correlation and collinearity statistics. The predictive powers of the GA-MLR models are studied using leave-one-out (LOO) cross-validation and external test set. The best quantitative structure-property relationship (QSPR) models are obtained based on the statistical parameters, such as R 2 , Q 2 LOO, and RMSE values for the data sets. The predictive ability of the GA-MLR models with two-three selected molecular descriptors was found to be satisfactory and could be used for modeling and predicting of the mentioned properties of nontested pyridine derivatives. K E Y W O R D S QSPR, pyridine derivatives, leave-one-out cross-validation, genetic algorithm-multiple linear regression

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“…But this method is only appropriate for hydrocarbon. The properties of the atom in molecule are correlative with the number of valence electrons and the number electron shells strongly, hence, in order to keep consistent with δ i , we defined the characteristic value of the atom(d i ) as: [4] , most of topological index were calculated according to structure diagram directly without interpretation.…”

Section: Molecular Descriptorsmentioning

confidence: 99%

“…A simple, economic and dependable method is in urgent need to estimated the toxicity of the substituted arenes. In recent years quantitative structure-activity relationship (QSAR) [1][2][3][4][5][6] has been proved to be a very important way to estimate and predict the bioactivity of the organic compounds [7] . In this article, we constructed a new connectivity index ( m D) based on Randic's branching degree index ( m χ) [8,9] .…”

Section: Introductionmentioning

confidence: 99%

The molecular topological research on acute toxicities of substituted arenes to aquatic organisms

Feng

Yan

Wei

et al. 2018

IOP Conf. Ser.: Earth Environ. Sci.

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Design, synthesis and 2D QSAR study of novel pyridine and quinolone hydrazone derivatives as potential antimicrobial and antitubercular agents

Cited by 83 publications

References 61 publications

Design and Construction of Aroyl‐Hydrazone Derivatives: Synthesis, Crystal Structure, Molecular Docking and Their Biological Activities

Design and Construction of Aroyl‐Hydrazone Derivatives: Synthesis, Crystal Structure, Molecular Docking and Their Biological Activities

Quantitative modeling for prediction of thermodynamic properties of some pyridine derivatives using molecular descriptors and genetic algorithm‐multiple linear regressions

The molecular topological research on acute toxicities of substituted arenes to aquatic organisms

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